Trifluoroacetic acid → HCID 54133431, compound

HRID 581778Notes

Reaction equation

HRID 581778 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]([C:20]1[CH:32]=[CH:31][C:23]([CH:24]=[CH:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:22][CH:21]=1)[CH2:16][CH2:17][O:18][CH3:19])=O)(C)(C)C>>[CH3:19][O:18][CH2:17][CH2:16][NH:15][C:20]1[CH:32]=[CH:31][C:23]([CH:24]=[CH:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:22][CH:21]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 53821831HCID 53821831, compound

Product 1

HCID 54133431HCID 54133431, compoundYield 70.7%

Procedure

Trifluoroacetic acid (3 ml) was added to ethyl 4-[N-tert-butoxycarbonyl-N-(2-methoxyethyl)amino]cinnamate (932 mg) in ice water bath and stirred for 15 minutes at same temperature. The solvent was evaporated under reduced pressure. The residue was partitioned between ethyl acetate and aqueous sodium bicarbonate solution. The organic layer was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel eluting to a mixture of n-hexane and ethyl acetate (3:1) and recrystallized from a mixture of n-hexane and ethyl acetate to give ethyl 4-(2-methoxyethylamino)cinnamate (470 mg) as crystals. mp: 49.9-53.4° C.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customThe residue was partitioned between ethyl acetate and aqueous sodium bicarbonate solution
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was chromatographed on silica gel eluting to a mixture of n-hexane and ethyl acetate (3:1)
  7. customrecrystallized from a mixture of n-hexane and ethyl acetate

Sources & evidence

ORD record
ord-96567c31123e450d9a155cc4cacd6f71
Source dataset
uspto-grants-1999_07
Patent number
US05922711

Reaction notes

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